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MedKoo Cat#: 597526 | Name: Homocitrulline
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Homocitrulline is an analogue of L-Citrulline, and is an amino acid that occurs in milk products.

Chemical Structure

Homocitrulline
Homocitrulline
CAS#1190-49-4

Theoretical Analysis

MedKoo Cat#: 597526

Name: Homocitrulline

CAS#: 1190-49-4

Chemical Formula: C7H15N3O3

Exact Mass: 189.1113

Molecular Weight: 189.22

Elemental Analysis: C, 44.43; H, 7.99; N, 22.21; O, 25.37

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Homocitrulline; NSC 27428; NSC-27428; NSC27428;
IUPAC/Chemical Name
N6-carbamoyl-L-lysine
InChi Key
XIGSAGMEBXLVJJ-YFKPBYRVSA-N
InChi Code
InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1
SMILES Code
N[C@@H](CCCCNC(N)=O)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
L-Homocitrulline is metabolized to homoarginine through homoargininosuccinate via the urea cycle pathway and its metabolic abnormality could lead to Lysinuric Protein Intolerance (LPI).
In vitro activity:
TBD
In vivo activity:
Lymphocytes isolated from Hcit-immunized mice had a significantly greater proliferative capacity compared with those from Cit-immunized mice or nonimmunized controls (p < 0.0001) (Fig. 3B). The culture supernatants from CD3-stimulated cells isolated from Hcit-immunized mice also contained significantly greater concentrations of IL-10 and -17 and IFN-γ compared with those of Cit-immunized mice or nonimmunized controls (Fig. 3C). Reference: J Immunol. 2010 Jun 15;184(12):6882-90. https://pubmed.ncbi.nlm.nih.gov/20488785/
Solvent mg/mL mM
Solubility
Water 100.0 528.50
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 189.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Mydel P, Wang Z, Brisslert M, Hellvard A, Dahlberg LE, Hazen SL, Bokarewa M. Carbamylation-dependent activation of T cells: a novel mechanism in the pathogenesis of autoimmune arthritis. J Immunol. 2010 Jun 15;184(12):6882-90. doi: 10.4049/jimmunol.1000075. Epub 2010 May 19. PMID: 20488785; PMCID: PMC2925534. 2. Viegas CM, Zanatta A, Knebel LA, Schuck PF, Tonin AM, Ferreira Gda C, Amaral AU, Dutra Filho CS, Wannmacher CM, Wajner M. Experimental evidence that ornithine and homocitrulline disrupt energy metabolism in brain of young rats. Brain Res. 2009 Sep 29;1291:102-12. doi: 10.1016/j.brainres.2009.07.021. Epub 2009 Jul 16. PMID: 19616520.
In vitro protocol:
TBD
In vivo protocol:
1. Mydel P, Wang Z, Brisslert M, Hellvard A, Dahlberg LE, Hazen SL, Bokarewa M. Carbamylation-dependent activation of T cells: a novel mechanism in the pathogenesis of autoimmune arthritis. J Immunol. 2010 Jun 15;184(12):6882-90. doi: 10.4049/jimmunol.1000075. Epub 2010 May 19. PMID: 20488785; PMCID: PMC2925534. 2. Viegas CM, Zanatta A, Knebel LA, Schuck PF, Tonin AM, Ferreira Gda C, Amaral AU, Dutra Filho CS, Wannmacher CM, Wajner M. Experimental evidence that ornithine and homocitrulline disrupt energy metabolism in brain of young rats. Brain Res. 2009 Sep 29;1291:102-12. doi: 10.1016/j.brainres.2009.07.021. Epub 2009 Jul 16. PMID: 19616520.
1: Turunen S, Hannonen P, Koivula MK, Risteli L, Risteli J. Separate and overlapping specificities in rheumatoid arthritis antibodies binding to citrulline- and homocitrulline-containing peptides related to type I and II collagen telopeptides. Arthritis Res Ther. 2015 Jan 9;17:2. doi: 10.1186/s13075-014-0515-z. PubMed PMID: 25573503; PubMed Central PMCID: PMC4320812. 2: Turunen S, Koivula MK, Risteli L, Risteli J. Ureido group-specific antibodies are induced in rabbits immunized with citrulline- or homocitrulline-containing antigens. Autoimmunity. 2016 Nov;49(7):459-465. Epub 2016 Apr 21. PubMed PMID: 27098309. 3: Lugli EB, Correia RE, Fischer R, Lundberg K, Bracke KR, Montgomery AB, Kessler BM, Brusselle GG, Venables PJ. Expression of citrulline and homocitrulline residues in the lungs of non-smokers and smokers: implications for autoimmunity in rheumatoid arthritis. Arthritis Res Ther. 2015 Jan 20;17:9. doi: 10.1186/s13075-015-0520-x. PubMed PMID: 25600626; PubMed Central PMCID: PMC4349479. 4: Jaisson S, Kerkeni M, Santos-Weiss IC, Addad F, Hammami M, Gillery P. Increased serum homocitrulline concentrations are associated with the severity of coronary artery disease. Clin Chem Lab Med. 2015 Jan;53(1):103-10. doi: 10.1515/cclm-2014-0642. PubMed PMID: 25153409. 5: Turunen S, Koivula MK, Melkko J, Alasaarela E, Lehenkari P, Risteli J. Different amounts of protein-bound citrulline and homocitrulline in foot joint tissues of a patient with anti-citrullinated protein antibody positive erosive rheumatoid arthritis. J Transl Med. 2013 Sep 23;11:224. doi: 10.1186/1479-5876-11-224. PubMed PMID: 24060405; PubMed Central PMCID: PMC3848878. 6: Turunen S, Huhtakangas J, Nousiainen T, Valkealahti M, Melkko J, Risteli J, Lehenkari P. Rheumatoid arthritis antigens homocitrulline and citrulline are generated by local myeloperoxidase and peptidyl arginine deiminases 2, 3 and 4 in rheumatoid nodule and synovial tissue. Arthritis Res Ther. 2016 Oct 20;18(1):239. PubMed PMID: 27765067; PubMed Central PMCID: PMC5072303. 7: Jaisson S, Kazes I, Desmons A, Fadel F, Oudart JB, Santos-Weiss IC, Millart H, Touré F, Rieu P, Gillery P. Homocitrulline as marker of protein carbamylation in hemodialyzed patients. Clin Chim Acta. 2016 Sep 1;460:5-10. doi: 10.1016/j.cca.2016.06.009. Epub 2016 Jun 11. PubMed PMID: 27302313. 8: Desmons A, Jaisson S, Pietrement C, Rieu P, Wynckel A, Gillery P. Homocitrulline: a new marker for differentiating acute from chronic renal failure. Clin Chem Lab Med. 2016 Jan;54(1):73-9. doi: 10.1515/cclm-2015-0398. PubMed PMID: 26124058. 9: Habib A, Md Yunus Z, Azize NA, Ch'ng GS, Ong WP, Chen BC, Hsu HT, Wong KJ, Pitt J, Ngu LH. Hyperexcretion of homocitrulline in a Malaysian patient with lysinuric protein intolerance. Eur J Pediatr. 2013 Sep;172(9):1277-81. doi: 10.1007/s00431-013-1947-1. Epub 2013 Jan 29. PubMed PMID: 23358709. 10: Jaisson S, Gorisse L, Pietrement C, Gillery P. Quantification of plasma homocitrulline using hydrophilic interaction liquid chromatography (HILIC) coupled to tandem mass spectrometry. Anal Bioanal Chem. 2012 Feb;402(4):1635-41. doi: 10.1007/s00216-011-5619-6. Epub 2011 Dec 12. PubMed PMID: 22160237. 11: Zanatta A, Viegas CM, Tonin AM, Busanello EN, Grings M, Moura AP, Leipnitz G, Wajner M. Disturbance of redox homeostasis by ornithine and homocitrulline in rat cerebellum: a possible mechanism of cerebellar dysfunction in HHH syndrome. Life Sci. 2013 Aug 6;93(4):161-8. doi: 10.1016/j.lfs.2013.06.013. Epub 2013 Jun 24. PubMed PMID: 23806752. 12: Turunen S, Koivula MK, Risteli L, Risteli J. Anticitrulline antibodies can be caused by homocitrulline-containing proteins in rabbits. Arthritis Rheum. 2010 Nov;62(11):3345-52. doi: 10.1002/art.27644. PubMed PMID: 20617522. 13: Zanatta Â, Rodrigues MD, Amaral AU, Souza DG, Quincozes-Santos A, Wajner M. Ornithine and Homocitrulline Impair Mitochondrial Function, Decrease Antioxidant Defenses and Induce Cell Death in Menadione-Stressed Rat Cortical Astrocytes: Potential Mechanisms of Neurological Dysfunction in HHH Syndrome. Neurochem Res. 2016 Sep;41(9):2190-8. doi: 10.1007/s11064-016-1933-x. Epub 2016 May 9. PubMed PMID: 27161368. 14: Metwalli AA, Lammers WL, Van Boekel MA. Formation of homocitrulline during heating of milk. J Dairy Res. 1998 Nov;65(4):579-89. PubMed PMID: 9839213. 15: Delporte C, Franck T, Noyon C, Dufour D, Rousseau A, Madhoun P, Desmet JM, Serteyn D, Raes M, Nortier J, Vanhaeverbeek M, Moguilevsky N, Nève J, Vanhamme L, Van Antwerpen P, Zouaoui Boudjeltia K. Simultaneous measurement of protein-bound 3-chlorotyrosine and homocitrulline by LC-MS/MS after hydrolysis assisted by microwave: application to the study of myeloperoxidase activity during hemodialysis. Talanta. 2012 Sep 15;99:603-9. doi: 10.1016/j.talanta.2012.06.044. Epub 2012 Jun 26. PubMed PMID: 22967600. 16: Al-Dirbashi OY, Al-Hassnan ZN, Rashed MS. Determination of homocitrulline in urine of patients with HHH syndrome by liquid chromatography tandem mass spectrometry. Anal Bioanal Chem. 2006 Dec;386(7-8):2013-7. Epub 2006 Oct 20. PubMed PMID: 17053917. 17: GERRITSEN T, VAUGHN JG, WAISMAN HA. The origin of homocitrulline in the urine of infants. Arch Biochem Biophys. 1963 Feb;100:298-301. PubMed PMID: 13960562. 18: Mydel P, Wang Z, Brisslert M, Hellvard A, Dahlberg LE, Hazen SL, Bokarewa M. Carbamylation-dependent activation of T cells: a novel mechanism in the pathogenesis of autoimmune arthritis. J Immunol. 2010 Jun 15;184(12):6882-90. doi: 10.4049/jimmunol.1000075. Epub 2010 May 19. PubMed PMID: 20488785; PubMed Central PMCID: PMC2925534. 19: Kraus LM, Miyamura S, Pecha BR, Kraus AP Jr. Carbamoylation of hemoglobin in uremic patients determined by antibody specific for homocitrulline (carbamoylated epsilon-N-lysine). Mol Immunol. 1991 Apr-May;28(4-5):459-63. PubMed PMID: 2062323. 20: Koshiishi I, Kobori Y, Imanari T. Determination of citrulline and homocitrulline by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1990 Oct 26;532(1):37-43. PubMed PMID: 2079537.